Dicyclohexylcarbodiimide → HCID 86688953, compound

HRID 404693Notes

Reaction equation

HRID 404693 reaction equation
[N:1]1([CH:7]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:41]12[CH2:48][CH2:47][CH:44]([CH2:45][CH2:46]1)[C@@H:43](O)[CH2:42]2>C1COCC1.CN(C=O)C>[N:1]1([CH:7]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[C:8]([O:10][C@@H:43]2[CH:44]3[CH2:47][CH2:48][N:41]([CH2:46][CH2:45]3)[CH2:42]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 43803863HCID 43803863, compound

Product 1

HCID 86688953HCID 86688953, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(piperidin-1-yl)-2-(thiophen-3-yl)acetic acid 21c (250 mg, 1.11 mmol), DCC (458 mg, 2.22 mmol), HOBT (340 mg, 2.22 mmol) and (R)-quinuclidin-3-ol (282 mg, 2.22 mmol) in dry THF (11.1 ml) and dry DMF (5.5 ml) was stirred at room temperature under nitrogen for 48 hours. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=97/3+0.3% NH4OH). The product was triturated with THF (10 ml) to obtain the title compound (217 mg, 58.5% yield) as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. customthe crude was purified by flash chromatography (DCM/MeOH=97/3+0.3% NH4OH)
  3. customThe product was triturated with THF (10 ml)

Sources & evidence

ORD record
ord-6aa558c0513d4a1e90e9b5f6d757e1c0
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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